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What's Been Your Biggest Career Risk/Experiment to Date?

So, I’m thinking of quitting freelancing. - Or at least significantly reigning in what services and how many orders I take on.

This is not an attack on Fiverr per-se. In this case, please don’t jump in with ‘why we all need to dump Fiverr and run’ arguments. In truth, I’m simply realizing that I don’t really like doing what I do anymore. It’s become far too stressful and time-consuming, and because of that, I feel a little burned out. As for what I’m think of doing instead, I’m thinking of experimenting with web design.

This is very ambitious since my professional web design skills amount to zero. However, I have discovered something of a niche in the market. Namely, that I could use my amazing domain name discovery skills and create websites on my own (not for clients) which I am quite good at, before selling these on places like Flippa.

As it is:

  • Even awful websites which aren’t on a par with what I can set up seem to sell for $1K - $5K
  • Few websites come already populated with SEO optimized content, whereas I can create all this
  • From recent experience, I can create a pretty neat website on a budget of $300 with an uninterrupted timescale of 2-3 weeks

So, my thinking at present is that I might try to shift from freelancing to creating and selling 1 x website per month in future.

Of course, I have no delusions that this will be as easy as I have just made out. To start I’m, therefore setting myself a goal of having my first website built and ready to go to market my the end of September. (Not the website I am working on at present). If it sells for a reasonable amount, I will then close down all my freelancing completely for 1 - 2 months and try to make and sell another.

Sadly, if my website didn’t sell, I would then likely have to go into battle mode to re-establish myself here and elsewhere. The risk there? 1 -2 months without a stable income stream could easily turn into 4 or more. In this case, implementing my entire strategy is going to be (potentially) very high risk.

All that said, risk is all part of the game and I think I could ride out a worst case scenario. What, though, is the biggest professional risk or career experiment you have taken to date? Did it pay off? Are you happy as a result? Or did it go wrong and did the sky fall in?

I’ll start by saying that mine was deciding to become a freelancer rather than a hotel manager. It paid off :slight_smile: But I’m still not mega rich and this causes me some heartache from time to time :frowning: .

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Pinned because it is the perfect “Weekend Topic”

My most significant risk was taking early retirement because the outside of the classroom stress of teaching was literally killing me. I felt like if I did not retire at the age of 62, I would be dead physically as well as mentally sooner than later. :weary:

Financially it was not a stellar move, but I have a pension I can live on if I am semi-frugal. Plus I have Fiverr. I use this income to buy the little extras I desire. :slightly_smiling_face:

It paid off in respect to the fact that I am so much happier now. No more boss dropping in and sitting down with his computer to type every word I said and then critique my lesson. (I always did well, but it stressed me that I would not.) No more parents who thought their child of average intelligence was secretly gifted and they misbehaved in class because they were bored. No more teaching related paperwork at night and on the weekends. :heart_eyes:

Another way it has paid off is in respect to my health. I slowly gained too much weight while I taught. Now my weight is slowly leaving me and I have more vim and vigor. :muscle:

No, the sky has not fallen in! But if it does I will go live with my kids. :laughing:

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This is how I feel about 35. It’s not freelancing per-se, I’ve just promised myself to be wealthy enough not to care about anything by 35. Then I can finally be a bee keeper.

I rarely talk about this but I was pretty much dead on legs by the end of 2012. My old job had become incredibly high-stress. As such, I didn’t have time to eat properly, do anything I actually liked doing, or even get a good nights sleep.

It got to the point where some kind of arthritis symptoms meant I couldn’t even twist the cap off a bottle. I just didn’t have time to really care. Anyway, I decided to try and freelance more because I knew that my old job would no longer exist in 5-years. That and I was already walking on eggshells by outing a bit of massive internal corruption/skullduggery. In the first few weeks, though, I started sleeping through until 11am like I was in a coma, and everything wrong with my health slowly fixed itself.

Now I I think I look and feel younger at 33 than I did at 27. Mainly due just to having time to eat better and take better care of myself.

The only trade-off is that I now have equivocal real-world people skills to those of a nuclear warhead. That’s not my fault, though. It’s the rest of the world which is borderline sociopathic. I just choose not to entertain its nonsense. :slight_smile:

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Awesome topic, sir!

My biggest risk was becoming a freelancer - I took voluntary redundancy from a well-paying middle-management job in the UK a few years back - I was offered a good severance package and since we were thinking of emigrating at the time, it made sense.

My wife was already a freelancer, and the city we moved to in the US (Asheville, NC) is notorious for not having great employment opportunities - it’s basically service industry, work for the local hospital, or bring your job with you.

When we moved here, I didn’t really have a “job” - I messed around with a few things - minor website building, trying to sell poetry (!), an Etsy store etc, but nothing really stuck. Towards the end of 2014 I was getting anxious about not having enough money, and was sinking into depression - I wrote about that here - For my own state-of-mind, I had to make a change.

Freelance writing was a natural extension of my skillset - I was a communications manager in IT before, and that combined with business, finance, and technology became my niche. I put up a website, started applying for jobs, and had the aim of making $100 a day. By the end of the year, I ended up making $200 a day. Since then I’ve been able to grow freelance writing to where I am pretty much constantly busy.

It was the most risky and the best career choice I ever made. The money is nice, but it’s the freedom that’s more important. The older I get (I am in my mid-40s now) the more I realize life is about how much time you have, not just how much money. It’s about freedom, taking pride in your work, and helping others. It’s about flexing those mental muscles and waking up each day looking forward to what’s ahead.

Recently though, I have started to get slightly itchy feet - I’ve been looking into what I really want to do with my life - why it matters, purpose, etc - y’know, usual mid-life crisis stuff :wink:

My main passions are around veganism and animal advocacy (and no, I don’t want to get into a debate about that :wink: ), so I have decided to pour more of my time into creating resources for vegans - it’s starting out as a passion project, but in the medium- to long-term I would love to monetize it in some way so that I can spend more of my time doing the things I truly care about.

Until then, my life is great - I have the career, friends, family, security, and attitudes that I want, but I am never averse to growing further. All in all, I think most risks are worth taking, so long as you ask the question “What’s the worst that could happen” and being prepared to live with the answer! Tim Ferriss has a great exercise called “Fear Setting” that really helps to put context around this stuff…

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This is such a great idea - the combination of a well-researched domain name, optimized keywords and SEO, is a great way to package up a website and sell it. Kudos on that.

My teacher friends tell me this is one of the most brutal parts of the job…

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Several too many for me but what else was I to do. Immediately upon completing my final year of college I began to search for work but wasn’t aware that my 1.5 years of admin experience wasn’t going to cut with any of the agencies in my area; especially the ones that claimed they trained. So after being backed into a barbed corner I went online and started completing odd jobs.

It worked for a while as I did earn some decent income; not much but enough buy essentials. Tried selling beauty products and that flopped while leaving me in the negative. Ventured into surveys and that did okay till the influx of site participants.

Then I tried my hand at writing articles online. It worked pretty well up till some discovered they could undermine the system which resulted in me not getting promoted. After an out of the blue change on a writing platform I was on it was decided that I should venture into blogging.

It’s an experience in itself especially when you have four going at once. I’m hanging onto fiverr as a side job to help ends meet. Freelancing is a big leap and the flooding of clients isn’t anything as was taught.

Discovering that you’re burned out is good and action should be taken. There are others that I follow on other platforms that experiencing the same thing and they had to make some difficult decisions to find a solution. Dealing with slight depression and hope my current summer plans will lighten the mood.

:coffee::pancakes:

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This is why freelancing/working for myself is the best career path for me. I hate urban life. I need to be not near to but in a remote, boring, place with nice natural surrounds to live. The only problem is, all those places are job-free zones.

So far, I have always located myself close to a bustling hotel/restaurant area where I can pick up work if need be. For October though, I’m ditching this rule for the quietest most boring village I can find which only has one shop and one (tiny) bar/restaurant.

Basically, I think I am more confident now.

My real dream in this regard, is to teach English in Cambodia but not like everyone else.

I want to get to the point where I have enough money not to care. Then I want to rock up in Cambodia, set up my own school, fit it out with tons of computers (but no wifi) and set up a language and skillset school. (Coding, designing, web design etc. Also, I wouldn’t hire transient backpacking teachers who had picked up their qualifications online for $150. Instead, I’d hire local successful people or people who are really passionate.

The way I see it, there is no point teaching everyone English without real work skills also.

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It’s a lot of effort to keep a blog up - I commend you on managing four of them!

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At present, I’m also moving into blogging. This year and last year, I scored a lot of regular work with some top blogs and I actually think this is what has burned me out creatively. My solution is to start monetizing my own content just like my clients are. The only problem is I’m a perfectionist. hence why this morning I started over again on my logo, as I suddenly realized that it’s awful. (Even though I still loved it yesterday).

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I dont know if that counts but,

I just got my first direct client, and im localizing a game.

at least to a newbie like me that feels like a huge step.

A pertinent thread. My own experience:

Leaving a relaxed, well paying job at IBM as a backend developer. Always found the job very boring and without substance(My opinion)(although the pay+perks were excellent). I was always fascinated and adored game development. From Ti-83+ calculators to Desktop computers, I loved developing games. I took the difficult decision of leaving IBM to pursue my own gaming studio. Now I work on Fiverr to fund my studio. My goal is to present my game at E3 some day. :slight_smile:

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Sweet, well timed post :wink::point_up_2: